Browsing by Subject "Cyclodextrin"

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Open Access
Antibacterial electrospun nanofibers from triclosan/cyclodextrin inclusion complexes
(Elsevier, 2014) Celebioglu A.; Umu, O. C. O.; Tekinay, T.; Uyar, Tamer
The electrospinning of nanofibers (NF) from cyclodextrin inclusion complexes (CD-IC) with an antibacterial agent (triclosan) was achieved without using any carrier polymeric matrix. Polymer-free triclosan/CD-IC NF were electrospun from highly concentrated (160% CD, w/w) aqueous triclosan/CD-IC suspension by using two types of chemically modified CD; hydroxypropyl-beta-cyclodextrin (HPβCD) and hydroxypropyl-gamma-cyclodextrin (HPγCD). The morphological characterization of the electrospun triclosan/CD-IC NF by SEM elucidated that the triclosan/HPβCD-IC NF and triclosan/HPγCD-IC NF were bead-free having average fiber diameter of 520±250nm and 1100±660nm, respectively. The presence of triclosan and the formation of triclosan/CD-IC within the fiber structure were confirmed by 1H-NMR, FTIR, XRD, DSC, and TGA studies. The initial 1:1molar ratio of the triclosan:CD was kept for triclosan/HPβCD-IC NF after the electrospinning and whereas 0.7:1molar ratio was observed for triclosan/HPγCD-IC NF and some uncomplexed triclosan was detected suggesting that the complexation efficiency of triclosan with HPγCD was lower than that of HPβCD. The antibacterial properties of triclosan/CD-IC NF were tested against Gram-negative (Escherichia coli) and Gram-positive (Staphylococcus aureus) bacteria. It was observed that triclosan/HPβCD-IC NF and triclosan/HPγCD-IC NF showed better antibacterial activity against both bacteria compared to uncomplexed pure triclosan.
Open Access
Antibacterial electrospun zein nanofibrous web encapsulating thymol/cyclodextrin-inclusion complex for food packaging
(Elsevier, 2017-10) Aytac Z.; Ipek, S.; Durgun, Engin; Tekinay, T.; Uyar, Tamer
Thymol (THY)/γ-Cyclodextrin(γ-CD) inclusion complex (IC) encapsulated electrospun zein nanofibrous webs (zein-THY/γ-CD-IC-NF) were fabricated as a food packaging material. The formation of THY/γ-CD-IC (1:1 and 2:1) was proved by experimental (X-ray diffraction (XRD), thermal gravimetric analysis (TGA), 1H NMR) and computational techniques. THY/γ-CD-IC (2:1) exhibited higher preservation rate and stability than THY/γ-CD-IC (1:1). It is worth mentioning that zein-THY/γ-CD-IC-NF (2:1) preserved much more THY as observed in TGA and stability of THY/γ-CD-IC (2:1) was higher, as shown by a modelling study. Therefore, much more THY was released from zein-THY/γ-CD-IC-NF (2:1) than zein-THY-NF and zein-THY/γ-CD-IC-NF (1:1). Similarly, antibacterial activity of zein-THY/γ-CD-IC-NF (2:1) was higher than zein-THY-NF and zein-THY/γ-CD-IC-NF (1:1). It was demonstrated that zein-THY/γ-CD-IC-NF (2:1) was most effective in inhibiting the growth of bacteria on meat samples. These webs show potential application as an antibacterial food packaging material.
Open Access
Antibacterial nanofibers of pullulan/tetracycline-cyclodextrin inclusion complexes for fast-disintegrating oral drug delivery
(Elsevier Inc., 2021-12-08) Hsiung, E.; Celebioglu, A.; Chowdhury, R.; Kilic, M. E.; Durgun, Engin; Altier, C.; Uyar, T.
Tetracycline is a widely used antibiotic suffering from poor water solubility and low bioavailability. Here, hydroxypropyl-beta-cyclodextrin (HPβCD) was used to form inclusion complexes (IC) of tetracycline with 2:1 M ratio (CD:drug). Then, tetracycline-HPβCD-IC was mixed with pullulan- a non-toxic, water-soluble biopolymer - to form nanofibrous webs via electrospinning. The electrospinning of pullulan/tetracycline-HPβCD-IC was yielded into defect-free nanofibers collected in the form of a self-standing and flexible material with the loading capacity of ∼ 7.7 % (w/w). Pullulan/tetracycline nanofibers was also generated as control sample having the same drug loading. Tetracycline was found in the amorphous state in case of pullulan/tetracycline-HPβCD nanofibers due to inclusion complexation. Through inclusion complexation with HPβCD, enhanced aqueous solubility and faster release profile were provided for pullulan/tetracycline-HPβCD-IC nanofibers compared to pullulan/tetracycline one. Additionally, pullulan/tetracycline-HPβCD-IC nanofibers readily disintegrated when wetted with artificial saliva while pullulan/tetracycline nanofibers were not completely absorbed by the same simulate environment. Electrospun nanofibers showed promising antibacterial activity against both gram-positive and gram-negative bacteria. Briefly, our findings indicated that pullulan/tetracycline-HPβCD-IC nanofibers could be an attractive material as orally fast disintegrating drug delivery system for the desired antibiotic treatment thanks to its promising physicochemical and antibacterial properties.
Open Access
Catechin encapsulated antioxidant electrospun nanofibers: A comparative study between cyclodextrin complex nanofibers and poly(vinyl alcohol) nanofibers
(American Chemical Society, 2023-05-31) Yıldız, Zehra İrem; Topuz, Fuat; Uyar, Tamer
Catechin is a plant polyphenol with a strong antioxidant effect. However, its use is limited due to its poor water solubility and sensitivity to light and oxygen. Here, catechin could be solubilized by inclusion complexation with cyclodextrin (CD) (CD-IC), and their solutions were electrospun into fibers in the presence and absence of poly(vinyl alcohol) (PVA) to compare the stabilization of catechin for its antioxidant activity. The antioxidant activity of catechin/CD IC nanofibers was also compared to that of the powder form. Scanning electron microscopy (SEM) analysis revealed the production of bead-free nanofibers. The successful incorporation of catechin into nanofibers was confirmed by Fourier-transform infrared spectroscopy (FTIR) analysis of catechin CC bond stretching. Likewise, 1H NMR spectroscopic analysis revealed the characteristic aromatic protons of catechin. The formation of inclusion complexes was confirmed by X-ray diffraction (XRD) and dissolution testing by the disappearance of crystalline peaks and rapid fiber dissolution, respectively. Finally, antioxidant testing demonstrated the higher antioxidant activity of polymer-free CD-IC nanofibers.
Open Access
Colon targeted delivery of niclosamide from β-cyclodextrin inclusion complex incorporated electrospun Eudragit® L100 nanofibers
(Elsevier BV, 2021-01) Çoban, Ö.; Aytaç, Zeynep; Yıldız, Zehra İrem; Uyar, Tamer
Electrospun nanofibers incorporated with inclusion complex (IC) of niclosamide (NIC) and hydroxypropyl-beta-cyclodextrin (HPβCD) (NIC-HPβCD-IC) was produced from pH-responsive polymer (Eudragit® L100, EUD), which disintegrates at pH values higher than 6, (EUD-NIC-HPβCD-IC-NF) for targeted delivery of NIC to the colon. Pristine EUD nanofibers (EUD-NF), only NIC loaded (EUD-NIC-NF) and physical mixture of NIC and HPβCD loaded EUD nanofibers (EUD-NIC-HPβCD-NF) were also produced as reference. SEM images revealed the bead-free and uniform morphology of nanofibers. XRD, TGA, and DSC were also performed for both NIC-HPβCD-IC and electrospun nanofibers and it was seen that there are some NIC molecules, which cannot make IC. Dissolution studies were carried out for 240 min at pH 1.2 and pH 7 simulating stomach and colon, respectively. EUD-NIC-NF released almost 53 % of NIC in 120 min, whereas EUD-NIC-HPβCD-NF (15 %) and EUD-NIC-HPβCD-IC-NF (8 %) released at most 15 % of NIC in 120 min. Then, remained NIC in the nanofibers released into the colon for the next 120 min. The slight difference in the release of NIC into stomach from EUD-NIC-HPβCD-NF and EUD-NIC-HPβCD-IC-NF might be due to the uncomplexed NIC molecules in EUD-NIC-HPβCD-IC-NF. More importantly, EUD-NIC-HPβCD-IC-NF was quite effective for preventing the release of NIC in the stomach in contrast to EUD-NIC-NF, which has already released more than half amount of NIC in 120 min. In conclusion, this study might open new areas for developing targeted delivery systems by the combination of nanofibers and CD-ICs for hydrophobic drugs such as NIC.
Open Access
Crosslinked PolyCyclodextrin/PolyBenzoxazine electrospun microfibers for selective removal of methylene blue from an aqueous system
(Elsevier, 2019) Doğan, Yelda Ertaş; Satılmış, Bekir; Uyar, Tamer
In this study, a blend solution of hydroxypropyl-β-cyclodextrin (HPβCD) and benzoxazine monomer (BA-a) was prepared in dimethylformamide to obtain HPβCD/BA-a microfibers by electrospinning technique. The electrospun HPβCD/BA-a microfibers were then thermally cured to obtain crosslinked PolyHPβCD/PolyBA-a microfibers. The compositions of HPβCD (120%, w/v) and BA-a (25%, w/v) were determined as an optimum concentration for producing bead-free and uniform microfibers from blend of HPβCD and BA-a (HPβCD/BA-a). Afterwards, the HPβCD/BA-a microfibers were thermally cured using step-wise curing method to obtain water-insoluble crosslinked PolyHPβCD/PolyBA-a fibrous membrane (FM). However, the fibrous structure of PolyHPβCD/PolyBA-a membrane was subjected to some morphological deformation during thermal curing. Therefore, citric acid (CTR, 5% and 15%, w/v) was incorporated into blend of HPβCD15/BA-a and it was named as HPβCDx/BA-a where x represents the amount of CTR (w/v) in the system. Blend solution of HPβCD15/BA-a was electrospun into microfibers to facilitate the crosslinking and to improve thermal resistance of the crosslinked fibrous membrane (PolyHPβCD15/PolyBA-a). Structural changes and thermal properties of the microfibers before and after curing were studied. Scanning electron microscopy was further used to monitor the morphology and stability of crosslinked PolyHPβCD/PolyBA-a microfibers in water and organic solvents. Consequently, PolyHPβCD15/PolyBA-a microfibers showed an enhanced structural stability in water and organic solvents along with thermal resistance, indicating successful crosslinking. Afterwards, the molecular separation ability of self-standing PolyHPβCD15/PolyBA-a FM was evaluated using dye mixture of Methylene Blue (MB) and Methyl Orange (MO). While both dye molecules are able to form a host-guest interaction between cyclodextrin molecules, crosslinked PolyHPβCD15/PolyBA-a FM showed sorption selectivity against cationic MB dye due to favorable electrostatic attractions between MB and HPβCD compared to anionic MO dye and HPβCD. In addition to selective sorption behavior of MB dye over MO dye, crosslinked PolyHPβCD15/PolyBA-a FM exhibited a decent adsorption capacity for MB in water.
Open Access
Cyclodextrin functionalized nanofibers via electrospinning
(2014) Çelebioğlu, Aslı
Electrospinning is a commonly studied and widely applied technique for generating nanofibers, with a diameter ranging from several tens of nanometers to a few micrometers. The low-cost, simple set-up, relatively high production rate and reproducibility increase the interests on this method in both academia and industry. Electrospun nanofibers are produced from a broad range of materials with extremely high surface area, very light-weight, nano-porous features and distinct physical/mechanical properties. The general talk in this technique focuses on the production of nanofibers from polymer base materials. However, very recent studies demonstrated that, it is also possible to obtain nanofibers from non-polymeric systems. For this novel development in electrospinning researches, we have achieved to generate nanofibers from cyclodextrins (CD) without using a polymeric template. CD are cyclic oligosaccharides consisting of α-(1,4)-linked glucopyranose units. The truncated cone shape structure of CD provides a favorable place for various kinds of organic molecules to form non-covalent host-guest inclusion complexes (IC). The enhancements and progressing at the guest molecules property and situation, creating with the inclusion complexation, make CD applicable in variety of areas including filtration, pharmaceuticals, cosmetics, functional foods, textiles, analytic chemistry etc. In this thesis, we report on the electrospinning of CD nanofibers, represent their functionalization and potential applications. Firstly, we produced CD nanofibers from three different chemically modified CD types (hydroxypropyl-β-cyclodextrin (HPβCD), hydroxypropyl-γ-cyclodextrin (HPγCD) and methyl-β-cyclodextrin (MβCD)). Afterwards, the electrospinning of native CD (α-CD, β-CD and γ-CD) nanofibers was achieved. The molecular entrapment capability of CD nanofibers was shown by capturing toxic volatile organic compounds (VOCs) from the surrounding. As the next step, the polymer-free nanofibers were obtained from the cyclodextrin inclusion complexes (CD-IC) with antibacterial agent, vanillin and essential oils. Here, we have also indicated applicability of CD-IC nanofibers as a result of antibacterial test. The functionalization of the CD nanofibers was continued with the green and one-step synthesis of metal nanoparticles (Ag-NP, Au-NP and Pd-NP) incorporated nanofibers, in which CD were used as reducing, stabilizing agent and fiber template. Even, the antibacterial, SERS and catalyst potential of these CD based nanofibers were demonstrated for the related nanoparticles. Our research is expanded to a new stage by the production of insoluble poly-CD nanofibers. We have worked on different crosslinking agents to attain insoluble poly-CD nanofibers with uniform morphology. After the optimization of poly-CD nanofibers, the most durable polyCD nanowebs were selected for further analysis and evaluation of the filtration performance in liquid environment. Within poly-CD nanofibers, we have eliminated the solubility challenge of CD nanofibers that restrict their usage. So, we assume that, poly-CD nanofibers will lead-up to generation of new advances for practices of CD nanofibers. All studies showed that, the self-assembly and self-aggregation property of CD are the prior requirements for the electrospinnability of these small molecules. To conclude, very intriguing materials were obtained by integrating large surface area of nanofibers with specific host-guest inclusion complexation capability and non-toxic, biocompatible nature of the CD. Moreover, CD molecules, which are generally used in the powder form, were rendered into more applicable nanofibers form that will represent ease during their usage.
Open Access
Cyclodextrin functionalized poly(methyl methacrylate) (PMMA) electrospun nanofibers for organic vapors waste treatment
(Elsevier BV, 2010) Uyar, Tamer; Havelund, R.; Nur, Y.; Balan, A.; Hacaloglu, J.; Toppare, L.; Besenbacher, F.; Kingshott, P.
Poly(methyl methacrylate) (PMMA) nanofibers containing the inclusion complex forming betacyclodextrin (_-CD) were successfully produced by means of electrospinning in order to develop functional nanofibrous webs for organic vapor waste treatment. Electrospinning of uniform PMMA nanofibers containing different loadings of _-CD (10%, 25% and 50% (w/w)) was achieved. The surface sensitive spectroscopic techniques; X-ray photoelectron spectroscopy (XPS) and time-of-flight secondary ion mass spectrometry (ToF-SIMS) showed that some of the _-CD molecules are present on the surface of the PMMA nanofibers, which is essential for the trapping of organic vapors by inclusion complexation. Direct pyrolysis mass spectrometry (DP-MS) studies showed that PMMA nanowebs containing _-CD can entrap organic vapors such as aniline, styrene and toluene from the surroundings due to inclusion complexation with _-CD that is present on the fiber surface. Our study showed that electrospun nanowebs functionalized with cyclodextrinsmayhave the potential to be used as molecular filters and/or nanofilters for the treatment of organic vapor waste and air filtration purposes.
Open Access
Cyclodextrin short-nanofibers using sacrificial electrospun polymeric matrix for VOC removal
(Springer, 2018) Çelebioğlu, Aslı; Uyar, Tamer
Cyclodextrins (CD) are cyclic oligosaccharides that can form noncovalent host-guest inclusion complexes to yield intriguing supramolecular structures. Electrospinning of nanofibers from CD is challenging since they are small molecules, nonetheless, electrospun nanofibers from CD would be particularly attractive because of the distinctive properties obtained by combining the very large surface area of nanofibers along with the inclusion complexation capability of CD. Herein, we performed the electrospinning of native CD type (i.e. γ-CD) using a minimal amount of carrier polymeric matrix (polyethylene oxide (PEO)). Once, the uniform nanofibers were electrospun from γ-CD/PEO systems, the polymeric carrier matrix was selectively removed by simple washing procedure, at the end, γ-CD short-nanofibers were obtained. We observed that γ-CD short-nanofibers could remove volatile organic compounds (VOC) (i.e. aniline) due to the inclusion complexation capability whereas pristine γ-CD powder could not have the capability for the VOC removal.
Open Access
Cyclodextrin-assisted synthesis of tailored mesoporous silica nanoparticles
(Beilstein-Institut Zur Forderung der Chemischen Wissenschaften, 2018) Topuz, Fuat; Uyar, Tamer
Mesoporous silica nanoparticles (MSNs) have sparked considerable interest in drug/gene delivery, catalysis, adsorption, separation, sensing, antireflection coatings and bioimaging because of their tunable structural properties. The shape, size and pore structure of MSNs are greatly influenced by the type of additives used, e.g., solvent and pore-templating agent. Here, we studied the influence of cyclodextrin (CD) molecules on the formation of MSNs. The nanoparticles over 100 nm in diameter were synthesized by surfactant- templated, hydrolysis-polycondensation reactions in the presence of pristine CD (β-CD) or hydroxypropyl-functionalized CDs (HP-γ-CD and HP-β-CD). Depending on the formulation conditions, differently shaped MSNs, such as bean-like, spherical, ellipsoid, aggregate and faceted were generated. The morphology and size of MSNs varied with the CD-type used. Generally, spherical particles were obtained with β-CD, while a faceted morphology was observed for the particles synthesized using HP-CDs. The particle size could be tuned by adjusting the amount of CD used; increasing the CD concentration led to larger particles. MSNs synthesized in the presence of β-CD displayed a smaller particle size than those produced with HP-functional CDs. FTIR, TGA and solidstate 13C NMR demonstrated the adsorption of CDs on the particle surfaces. The proposed concept allows for the synthesis of silica nanoparticles with control over particle shape and size by adjusting the concentration of additives in a simple, one-pot reaction system for a wide range of applications.
Open Access
Cyclodextrin-functionalized mesostructured silica nanoparticles for removal of polycyclic aromatic hydrocarbons
(Academic Press Inc., 2017) Topuz, F.; Uyar, T.
Polycyclic aromatic hydrocarbons (PAHs) are the byproducts of the incomplete combustion of carbon-based fuels, and have high affinity towards DNA strands, ultimately exerting their carcinogenic effects. They are ubiquitous environmental contaminants, and can accumulate on tissues due to their lipophilic nature. In this article, we describe a novel concept for PAH removal from aqueous solutions using cyclodextrin-functionalized mesostructured silica nanoparticles (CDMSNs) and pristine mesostructured silica nanoparticles (MSNs). The adsorption applications of MSNs are greatly restricted due to the absence of surface functional groups on such particles. In this regard, cyclodextrins can serve as ideal functional molecules with their toroidal, cone-type structure, capable of inclusion-complex formation with many hydrophobic molecules, including genotoxic PAHs. The CDMSNs were synthesized by the surfactant-templated, NaOH-catalyzed condensation reactions of tetraethyl orthosilicate (TEOS) in the presence of two different types of cyclodextrin (i.e. hydroxypropyl-β-cyclodextrin (HP-β-CD) and native β-cyclodextrin (β-CD)). The physical incorporation of CD moieties was supported by XPS, FT-IR, NMR, TGA and solid-state 13C NMR. The CDMSNs were treated with aqueous solutions of five different PAHs (e.g. pyrene, anthracene, phenanthrene, fluorene and fluoranthene). The functionalization of MSNs with cyclodextrin moieties significantly boosted the sorption capacity (q) of the MSNs up to ∼2-fold, and the q ranged between 0.3 and 1.65 mg per gram CDMSNs, of which the performance was comparable to that of the activated carbon.
Open Access
Cyclodextrin-grafted electrospun cellulose acetate nanofibers via "Click" reaction for removal of phenanthrene
(Elsevier, 2014-06-30) Çelebioğlu, A.; Demirci, S.; Uyar, T.
Beta-cyclodextrin (p-CD) functionalized cellulose acetate (CA) nanofibers have been successfully prepared by combining electrospinning and "click" reaction. Initially, p-CD and electrospun CA nanofibers were modified so as to be azide-p-CD and propargyl-terminated CA nanofibers, respectively. Then, "click" reaction was performed between modified CD molecules and CA nanofibers to obtain permanent grafting of CDs onto nanofibers surface. It was observed from the SEM image that, while CA nanofibers have smooth surface, there were some irregularities and roughness at nanofibers morphology after the modification. Yet, the fibrous structure was still protected. ATR-FTIR and XPS revealed that, CD molecules were successfully grafted onto surface of CA nanofibers. The adsorption capacity of p-CD-functionalized CA (CA-CD) nanofibers was also determined by removing phenanthrene (polycyclic aromatic hydrocarbons, PAH) from its aqueous solution. Our results indicate that CA-CD nanofibers have potential to be used as molecular filters for the purpose of water purification and waste water treatment by integrating the high surface area of nanofibers with inclusion complexation property of CD molecules.
Open Access
Development of multifunctional nanofibrous materials via electrospinning
(2014) Kayacı, Fatma
Electrospun nanofibers are very attractive for many applications including functional textile, biomedical, energy, sensor, biotechnology, food packaging and filtration due to their large surface area to volume ratio, pores in nano range, high encapsulation efficiency, low basis weight and design flexibility for physical/chemical modification. Cyclodextrins (CD) are applicable in several industries such as pharmaceutical, cosmetic, textile, functional food and filtration owing to their intriguing ability to form non-covalent host-guest inclusion complexes (IC) with a variety of molecules. Furhermore, atomic layer deposition (ALD) technique can be effectively used to deposit metal oxides onto temperature-sensitive polymeric substrates. In this dissertation, initially, CD-IC of bioactive compounds (vanillin, eugenol, geraniol, triclosan) having antibacterial and/or antioxidant properties were incorporated into electrospun nanofibers via electrospinning. Higher thermal stability, controlled/sustained release, enhanced solubility and functionality of these compounds have been provided by CD-IC. These specific properties of CD-IC have been combined with high surface area and nanoporous structure of electrospun nanofibers. Thereby, the resulting functional nanofibrous materials can be quite applicable in active food packaging in order to prevent foodborne diseases by providing safety/quality of nutrition and extending shelf life of food. On the other hand, CD incorporated electrospun nanofibers have also been developed for efficient removal of unpleasant odors, hazardous organic waste molecules from air by taking advantages of not only high surface area and nanoporous structure of nanofibers but also IC capability of CD. Since CD are water soluble, CD polymer (CDP) coated onto nanofibers have been also obtained for molecular filtration of polyaromatic hydrocarbons from aqueous environment. Moreover, metal oxides (ZnO, TiO2) have been deposited onto electrospun nanofibers via ALD in order to develop efficient and energy saving innovative nanofibrous membrane materials for water purification and waste treatment. Thus, organic pollutants in water have been effectively disintegrated by photocatalytic activity of these nanofibrous filtering materials having high surface area. Overall, the multifunctional electrospun nanofibrous materials have been improved by incorporating CD-IC or CD into the fiber matrix; by coating either CDP or metal oxides (ZnO, TiO2) onto fiber surface to enhance possible applications of nanofibers for filtration, food packaging, functional textiles, etc.
Open Access
Drug delivery system based on cyclodextrin-naproxen inclusion complex incorporated in electrospun polycaprolactone nanofibers
(Elsevier, 2014) Canbolat, M. F.; Celebioglu A.; Uyar, Tamer
In this study, we select naproxen (NAP) as a reference drug and electrospun poly (e-caprolactone) (PCL) nanofibers as a fibrous matrix for our drug-delivery system. NAP was complexed with beta-cyclodextrin (βCD) to form inclusion complex (NAP-βCD-IC) and then NAP-βCD-IC was incorporated into PCL nanofibers via electrospinning. The incorporation of NAP without CD-IC into electrospun PCL was also carried out for a comparative study. Our aim is to analyze the release profiles of NAP from PCL/NAP and PCL/NAP-βCD-IC nanofibers and we investigate the effect of CD-IC on the release behavior of NAP from the nanofibrous PCL matrix. The characterization of NAP-βCD-IC and the presence of CD-IC in PCL/NAP-βCD-IC nanofibers were studied by FTIR, XRD, TGA, NMR and SEM. The SEM imaging of the electrospun PCL/NAP and PCL/NAP-βCD-IC nanofibers reveal that the average fiber diameter of these nanofibers is around 300. nm, in addition, the aggregates of CD-IC in PCL/NAP-βCD-IC nanofibers is observed. The release study of NAP in buffer solution elucidate that the PCL/NAP-βCD-IC nanofibers have higher release amount of NAP than the PCL/NAP nanofibers due to the solubility enhancement of NAP by CD-IC.
Open Access
Efficient encapsulation of citral in fast-dissolving polymer-free electrospun nanofibers of cyclodextrin inclusion complexes: High thermal stability, longer shelf-life, and enhanced water solubility of citral
(MDPI AG, 2018) Aytaç, Zeynep; Çelebioğlu, Aslı; Yildız, Zehra İrem; Uyar, Tamer
Here, we report a facile production of citral/cyclodextrin (CD) inclusion complex (IC) nanofibers (NFs) from three types of CDs (hydroxypropyl-beta-cyclodextrin (HPβCD), hydroxypropyl-gamma-cyclodextrin (HPγCD), and methylated-beta-cyclodextrin (MβCD)) by an electrospinning technique without the need of any polymeric carrier matrix. Self-standing nanofibrous webs of citral/CD-IC nanofibers (citral/CD-IC-NF) with uniform fiber morphology have been successfully electrospun from aqueous solutions of citral/CD-IC. Thanks to the inclusion complex formed with CDs, the efficient preservation of citral (up to ~80%) in citral/CD-IC-NFs was observed. In addition, the citral/CD-IC-NFs have shown ~50% preservation of citral for 15 days at room temperature even though citral has a highly volatile nature. The enhanced thermal stability of citral (~100-300◦C) in citral/CD-IC-NFs compared to pure citral (~50-165◦C) has been observed. Moreover, citral/CD-IC-NFs tended to disintegrate in water very quickly. To summarize, citral was efficiently encapsulated in citral/CD-IC-NFs, and these citral/CD-IC-NFs have been shown to be fast dissolving. In citral/CD-IC-NFs, citral/CD-ICs have enhanced water solubility of citral along with high-temperature stability and a longer shelf-life.
Open Access
Electrospinning of cyclodextrin functionalized nanofibers and their applications
(2016-08) Aytaç, Zeynep
Electrospinning is a widely used versatile method to produce nanofibers with high surface to volume ratio and porous structure. Owing to the unique properties, electrospun nanofibers are of great importance as a carrier matrix for drugs; antioxidant, and antibacterial agents, flavour/fragrances. Though polymers are material of choice for producing electrospun nanofibers, it is likely to obtain nanofibers from low molecular weight molecules. Cyclodextrin (CDs) are intriguing molecules having the capability of forming inclusion complex (IC) with numerous guest molecules such as drugs, food additives, flavour/fragrances, antioxidant and antibacterial agents. Therefore, CD-ICs enhance solubility, reduce volatility, and provide controlled release of the guest molecules. Integrating CD-ICs with electrospinning opens a new door to produce remarkable materials. In this thesis, nanofibers containing CD-ICs of bioactive agents including antioxidant/antibacterial and flavour/fragrance molecules were produced via electrospinning technique. Firstly, CD-ICs of antioxidant/antibacterial compounds (gallic acid, α-tocopherol, quercetin, and thymol) were synthesized and then, added into polylactic acid or zein solutions to produce CD-IC incorporated electrospun polymeric nanofibers. Afterwards, the release behavior, antioxidant and antibacterial activity of these nanofibers were investigated. In addition, the potential use of these nanofibers as active food packaging and delivery material was revealed by packing meat samples by these nanofibers. Secondly, electrospun nanofibers were developed as a releasing material from CD-ICs of volatile flavour/fragrance molecules (geraniol, limonene, and linalool) without using polymeric matrix. The preservation of volatile compounds is shown to be possible to a great extent with antibacterial CD-IC nanofibers. Furthermore, the shelf life of flavour/fragrance molecules has been enhanced at least 50 days by CD-IC nanofibers. Finally, for the first time in the literature core-shell nanofibers were designed by using CD-IC of curcumin, an antioxidant molecule and polylactic acid solutions as core and shell, respectively. The ability of core-shell nanofibers as a drug delivery carrier was suggested by release and antioxidant activity tests. To conclude, CD-IC incorporated electrospun nanofibers produced by three different approach is shown to be used as efficient material for various applications particularly for food packaging and drug delivery.
Open Access
Electrospinning of cyclodextrin/linalool-inclusion complex nanofibers: fast-dissolving nanofibrous web with prolonged release and antibacterial activity
(Elsevier, 2017-09) Aytac Z.; Yildiz, Z. I.; Kayaci-Senirmak, F.; Tekinay, T.; Uyar, Tamer
The volatility and limited water solubility of linalool is a critical issue to be solved. Here, we demonstrated the electrospinning of polymer-free nanofibrous webs of cyclodextrin/linalool-inclusion complex (CD/linalool-IC-NFs). Three types of modified cyclodextrin (HPβCD, MβCD, and HPγCD) were used to electrospin CD/linalool-IC-NFs. Free-standing CD/linalool-IC-NFs facilitate maximum loading of linalool up to 12% (w/w). A significant amount of linalool (45–89%) was preserved in CD/linalool-IC-NFs, due to enhancement in the thermal stability of linalool by cyclodextrin inclusion complexation. Remarkably, CD/linalool-IC-NFs have shown fast-dissolving characteristics in which these nanofibrous webs dissolved in water within two seconds. Furthermore, linalool release from CD/linalool-IC-NFs inhibited growth of model Gram-negative (E. coli) and Gram-positive (S. aureus) bacteria to a great extent. Briefly, characteristics of liquid linalool have been preserved in a solid nanofiber form and designed CD/linalool-IC-NFs confer high loading capacity, enhanced shelf life and strong antibacterial activity of linalool.
Open Access
Electrospinning of nanocomposite nanofibers from cyclodextrin and laponite
(Elsevier, 2018) Topuz, Fuat; Uyar, Tamer
Herein, the electrospinning of nanocomposite nanofibers from a non-polymeric system using cyclodextrin (CD)and Laponite was reported. Laponite, a hectorite-type synthetic clay, was used as an additive in the aqueoussolutions of CD molecules, and its influence on the polymer-free electrospinning of CD was investigated. Flowtests showed that the viscosity of CD solutions increased with a Laponite content rise at low shear rates and anunequalled degree of shear thinning at high shear rates. The morphology of the CD/Laponite nanofibers wasexplored by SEM, which revealed the formation of smooth nanofibers at low Laponite content (0.62 wt%) andnon-smooth nanofibers at Laponite content over 1.56 wt% due to enhanced electrostatic interactions betweenthe charged surface of Laponite and hydroxyl groups of CD. Further increasing Laponite content to 12.5 wt% ledto only micro-sized beads instead offibers due to electrospraying, suggesting that the embedded Laponite sig-nificantly disturbed hydrogen bonds among CD molecules. The presence of Laponite in the nanofibers wasconfirmed over chemical analysis by EDX and XPS. TEM analysis displayed homogeneous distribution of theexfoliated Laponite in the CD nanofibers, as supported by the disappearance of the diffraction patterns ofLaponite by WAXS. The nanocomposite CD/Laponite mats with Laponite content of≤1.56 wt% maintained theirself-standing andflexible structure to some extent, as revealed by tensile tests. In brief, this study reports thepolymer-free electrospinning of nanocomposite nanofibers based on CD and Laponite and investigates the impactof the incorporated clay on the polymer-free electrospinning of CD molecules.
Open Access
Electrospinning of nanofibers from non-polymeric systems : electrospun nanofibers from native cyclodextrins
(Elsevier, 2013) Çelebioğlu, Aslı; Uyar, Tamer
Electrospinning of nanofibers from non-polymeric systems is rather challenging, yet in this study, we have successfully performed electrospinning of nanofibers from two of the native cyclodextrins (CDs); α-CD and β-CD. Electrospinning was carried out for highly concentrated solutions of α-CD (120% up to 160%, w/v) and β-CD (120% up to 150%, w/v) in basic aqueous system. At optimal concentration level, the electrospinning of CD solutions yielded bead-free uniform CD nanofibers without using carrier polymeric matrix. Similar to polymeric systems, the electrospinning of CD solutions resulted in different morphologies and average fiber diameters depending on the CD type and CD concentration. The dynamic light scattering (DLS) and rheology measurements were performed in order to examine the electrospinnability of CD solutions. The existence of CD aggregates via hydrogen bonding and very high solution viscosity and viscoelastic solid-like behavior of CD solutions were found to be the key factors for obtaining bead-free nanofibers from CDs. The addition of urea disrupted CD aggregates and lowered the viscosity significantly, and therefore, the urea-added CD solutions yielded beaded fibers and/or beads. Although the as-received CDs in powder form are crystalline, the structural analyses by XRD and HR-TEM indicated that electrospun CD nanofibers have amorphous characteristic without showing any particular orientation or crystalline aggregation of CD molecules.
Open Access
Electrospun nanofibers from cyclodextrin inclusion complexes with cineole and p-cymene: Enhanced water solubility and thermal stability
(Blackwell Publishing, 2018) Çelebioğlu, Aslı; Yıldız, Zehra İrem; Uyar, Tamer
The electrospinning of self-standing nanofibrous webs from inclusion complexes (IC) of cineole and p-cymene with two modified cyclodextrins (HPβCD, HPγCD) was achieved without using carrier polymeric matrix. Although they are highly volatile, certain amount of cineole and p-cymene was protected in cyclodextrin inclusion complexes nanofibers (CD-IC-NF). That is, 68.4%, 78.1%, 54.5% and 44.0% (w/w) of active agent were preserved in cineole/HPβCD-IC-NF, cineole/HPγCD-IC-NF, p-cymene/HPβCD-IC-NF and p-cymene/HPγCD-IC-NF, respectively. Remarkable, high thermal stability for cineole (~150 °C - 270 °C) and p-cymene (~150 °C - 275 °C) was achieved for CD-IC-NF samples due to CD-IC formation. The water solubility of cineole and p-cymene was significantly improved by inclusion complexation where CD-IC-NF samples become readily dissolved in water. In brief, essential oils and flavours such as cineole and p-cymene could be applicable in food and oral care applications owing to their fast-dissolving behaviour along with high water solubility, enhanced thermal stability and free-standing feature of CD-IC-NF webs.